Abstract
A range ofcis- andtrans-monoenoic fatty acids was tested as substrates for desaturation in microsomal preparations from rat liver.Trans-monoenoic acids were generally desaturated in the Δ9 position to the same extent as stearic acid. Acids with Δ7-trans- and Δ11-trans-olefinic unsaturation produced Δ7-trans,9-cis- and Δ9-cis,11-trans-conjugated dienoic acids, respectively, but the Δ8-trans- and Δ10-trans-monoenoic acids did not give Δ8,9- or Δ9,10-allenes. Of thecis-monoenoic acids examined, only those with double bonds at or beyond the Δ14 position gave any measurable Δ9 desaturation. When Δ9 desaturation of long chain saturated acids was inhibited by adding sterculic acid, these saturated acids were desaturated at the Δ5 and Δ6 positions. Many of the monoenoic acids tested were also desaturated at the Δ5 and/or Δ6 positions, although the percentage conversions were always low. Δ9-cis,11-trans-, Δ9-cis,12-trans- and Δ9-cis,13-trans-dienoic acids, produced in situ by Δ9 desaturation of the corresponding monoenoic acids, were extensively desaturated in the Δ6 position. These results are discussed in terms of: (a) the various models proposed to explain the substrate specificities of the desaturases, and (b) the metabolism of unnatural fatty acids ingested from dietary sources.
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Strittmatter, P., L. Spatz, D. Corcoran, M.J. Rogers, B. Setlow, and R. Redline, Proc. Natl. Acad. Sci. USA 71:4565 (1974).
Enoch, H.G., A. Catala, and P. Strittmatter, J. Biol. Chem. 251:5095 (1976).
Brett, D., D. Howling, L.J. Morris, and A.T. James, Arch. Biochem. Biophys. 143:535 (1971).
James, A.T., in “Function and Biosynthesis of Lipids,” Edited by N.G. Bazan, R.R. Brenner, and N.M. Glusto, Plenum Publishing Corp., New York, NY, 1977, p. 51.
Morris, L.J., R.V. Morris, W. Kelly, and A.T. James, Biochem. J. 109:673 (1968).
Johnson, A.R., and M.I. Gurr, Lipids 6:78 (1971).
Paulsrud, J.R., S.E. Stewart, G. Graff, and R.T. Holman, Lipids 5:611 (1970).
Gurr, M.I., M.P. Robinson, A.T. James, L.J. Morris, and D. Howling, Biochim. Biophys. Acta 280:419 (1972).
Fulco, A.J., and J.F. Mead, J. Biol. Chem. 235:3379 (1960).
Brenner, R.R., Lipids 6:567 (1971).
Houtsmuller, U.M.T., Fette Seifen Anstrichm. 80:162 (1978).
Gunstone, F.D., C.M. Scrimgeour, and H.S. Vedanayagam, J. Chem. Soc. (Commun.) 916 (1974).
Crossland, R.K., and K.L. Servis, J. Org. Chem. 35:3195 (1970).
Barve, J.A., and F.D. Gunstone, Chem. Phys. Lipids 7:311 (1971).
Lindlar, H., Helv. Chim. Acta 35:340 (1952).
Gunstone, F.D., and M. Lie Ken Jie, Chem. Phys. Lipids 4:1 (1970).
Stoffel, W., Justus Liebigs Ann. Chemie 673:26 (1964).
Von Rudloff, E., J. Am. Oil Chem. Soc. 33:126 (1956).
James, A.T., P. Harris, and J. Bezard, Eur. J. Biochem. 3:318 (1968).
Brindley, D.N., and G. Hubscher, Biochim. Biophys. Acta 106:495 (1965).
James, A.T., and E.A. Piper, Anal. Chem. 35:515 (1963).
Gurr, M.I., and M.P. Robinson, Anal. Biochem. 47:146 (1972).
Brenner, R.R., Mol. Cell. Biochem. 3:41 (1974).
Inkpen, C.A., R.A. Harris, and F.W. Quackenbush, J. Lipid Res. 10:277 (1969).
Bernert, J.T., and H. Sprecher, Biochim. Biophys. Acta 398:354 (1975).
Pollard, M.R., The Synthesis,13C Nuclear Magnetic Resonance Spectroscopy, and Enzymic Desaturation of Some Unsaturated Fatty Acids, Ph.D. Thesis, University of St. Andrews, Scotland (1977).
Jamieson, F.R., in “Topics in Lipid Chemistry,” Vol. 1, Ch. 3, Edited by F.D. Gunstone, Logos Press, (1969).
Lie Ken Jie, M.S.F., Synthesis and Properties of some Unsaturated Acids and their Derivatives, Ph.D. Thesis, University of St. Andrews, Scotland, (1968).
Lemarchal, P., and M. Bornens, Bull. Soc. Chim. Biol. 50:195 (1968).
Jeffcoat, R., and M.R. Pollard, Lipids 12:480 (1977).
Lippel, K., F.D. Gunstone, and J.A. Barve, Lipids 8:119 (1973).
Lippel, K., D. Carpenter, F.D. Gunstone, and I.A. Ismail, Lipids 8:124 (1973).
Cook, H.W., and M.W. Spence, Biochim. Biophys. Acta 369:129 (1974).
Quint, J.F., and A.J. Fulco, J. Biol. Chem. 248:6885 (1973).
Scholfield, C.R., V.L. Davison, and H.J. Dutton, J. Am. Oil Chem. Soc. 44:648 (1967).
Carpenter, D.L., and H.T. Slover, J. Am. Oil Chem. Soc. 50:372 (1973).
Wood, R., F. Chumbler, and R. Wiegand, J. Biol. Chem. 252:1965 (1977).
Morrison, W.R., in “Topics in Lipid Chemistry,” Vol. 1, Ch. 2, Edited by F.D. Gunstone, Logos Press (1969).
Viviani, R., Adv. Lipid Res. 8:268 (1970).
Guo, L.S.S., and J.C. Alexander, Biochim. Biophys. Acta 369:411 (1974).
Anderson, R.L., C.S. Fullmer, and E.J. Hollenbach, J. Nutr. 105:393 (1975).
Privett, O.S., E.M. Stearns, and E.C. Nickell, J. Nutr. 92:303 (1967).
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Pollard, M.R., Gunstone, F.D., James, A.T. et al. Desaturation of positional and geometric isomers of monoenoic fatty acids by microsomal preparations from rat liver. Lipids 15, 306–314 (1980). https://doi.org/10.1007/BF02533545
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DOI: https://doi.org/10.1007/BF02533545